Preliminary results by the principal investigator indicate that the (3.3) - sigmatropic rearrangement of allylic and propargylic imidate derivatives should afford new and versatile routes to a variety of alkaloids. In particular total synthesis of alkaloids with 1-azaspiro ring systems (e.g. histrionicotoxin), cis-perhydroquinoline ring systems (e.g. pulmiliotoxin C), and substituted pyridone ring systems (e.g. cytisine) will be investigated. BIBLIOGRAPHIC REFERENCES: "A New Synthesis of 2-Pyridones. Solution Thermolysis of Propargylic Pseudoureas," Journal of the American Chemical Society, in press (1977) L.E. Overman and S. Tsuboi. "A Short Stereospecific Total Synthesis of dl-Pumiliotoxin C," Tetrahedron Letters, in press (1977) L.E. Overman and P.J. Jessup.